Two Black Cadillacs
by mischief-maker1
Summary: When he is caught cheating on his wife, his wife and mistress conspire against him. Rated M to be safe. Major character death.


**Disclaimer: sorry, Supernatural isn't mine. Oh how I wish it was...**

Author Note: hi guys! So...if you're reading my other two fics, I'm sorry, I just had to get this one out. It's based on the song "Two Black Cadillacs" by Carrie Underwood. If you haven't heard it, that's okay. It's just the basis for fic. I left it vague on purpose. I wanted to surprise you with a few things.

 **Warnings: talks of murder, violence toward women (slightly) mentions of abortion. That's about it. Little to no smut, dark themes.**

 **Here ya go...**

* * *

The phone call jarred him out of his sleep. "Yeah?" he growled groggily.

"Winchester...there's been an accident. Your brother..."

"Oh God," he muttered as he looked at his wife, whose face was full of concern. "Is he..."

He could practically hear the wince from the woman at the other end. "He died in route to the hospital," Jo told him.

"No!"

Jo's voice was full of concern as she said, "I'm so sorry. I just finished my shift. I rode with him on the bus. We tried everything."

"Him and that damn car...was he showboating?"

"I don't know. I just...its totaled. Do you want me to have it towed to the shop? I'll call in a favor."

He just...he couldn't function. It had always been "Those damn Winchester boys," as long as he could remember. To be just him...

"Hey! You okay?"

He blinked. "No. I-I'll..." he cleared his throat. "I don't know what to do."

"Call me if you need me," she told him softly before she hung up the phone.

He swallowed hard and looked at his wife. "He's dead. I just..." he registered her sorrow filled eyes before he checked out.

Three days...it had been three days since he'd been alone in the world. Sure, he had his wife, his sons, his baby girl...but to lose his brother...the one that had been by his side, through their mother's death, through the abuse of a drunk for a father, being put through the system until Jo's parents, Bobby and Ellen Singer had taken them in and fostered them before they'd finally adopted them, but let them keep their last name, through colleges and girlfriends and marriages, births, deaths, he couldn't believe it.

He heard feet pounding on the stairs and his son was in the doorway. "Dad? You about ready?"

He blew out a breath as he adjusted his tie. He hated ties. He wore one almost every day for work, but that didn't mean he liked it. "Yeah, bud, I'm about ready." He blew out another breath and looked himself over once more in the mirror. He'd turned forty a few months ago, and though his hair was salt and pepper, and he wasn't quite in as good a shape he'd been in during his twenties, he still got the glances from the little chickadees that flitted around at work. His brother would never get another birthday. The thought was more than a little sobering.

His wife came in then. "Limo's here."

He gave her a half smile. "Remember the last time we rode in a limo?"

She smirked. "Pretty sure that's when Little Miss was conceived."

His smile grew as he remembered that night. "We had such a blast."

"Well why not? It isn't every day someone makes the cover of a magazine, honey."

His smile faltered and she was by his side in an instant as a tear rolled down his cheek. She took him in her arms and guided him to the bed as she pulled his head down to her shoulder. He still remembered the day they met. He had a chip on his shoulder a mile wide, and was just a general asshole. She had seen through his facade and befriended him anyway. He'd opened up to her like he had only one other person in his life. They'd become friends. When it blossomed into something more, she decided to go to the same college as him, and that day, their senior year, when the pregnancy test came back positive, he'd dropped to one knee, because he knew he couldn't live without her anyway.

"We'll make it through this. Think of all we've faced together."

He sighed and nodded. "I know. I just..."

She patted his knee. "It'll be okay."

He sucked in a breath. "Let's go get this over with."

They walked downstairs where everyone was waiting. He glanced over at his brother's wife. She'd been a rock through this whole thing. They were both career driven, eager enough to spoil their niece and nephews. He wondered if she regretted them not having kids now. But he walked over to her and hugged her. "You okay?" he asked.

She just nodded solemnly. "He died in his car. What more can you say? He loved that car as much as he loved me."

He nodded. His brother had formed an almost romantic attachment to that car. It was funny, everyone had teased him in high school, but it was his brother that hadn't been able to let go of the car. And why not? It was a gorgeous piece of machinery. "Jo had it towed to the shop. I'm sure Bobby can..."

Her eyes turned cold. "Burn the fucking thing. Crunch it. Leave it to rot for all I care."

He swallowed hard, but nodded. "Sure. Uh...whatever."

She put a hand on his arm. "I'm sorry. I just..."

He put his hand on top of hers. "I know, Jess. I know. I just can't believe Sam's gone..."

* * *

RUBY POV

TWO MONTHS BEFORE...

She worried the piercing in her lip as she waited. When the woman called and said she was Sam's wife, well, Ruby had been more than a little surprised. Sam worked at the law firm down the street from the coffee shop Ruby's sister, Lilith, owned. Ruby worked at the tattoo parlor down the way and visited Lil quite often. He used to come in all the time with his lawyer buddies. He'd flirt, she'd flirt back. It became a thing. Then, about a year before, it turned into something more. But he'd never said he was married. She had a damn code. Her sister was the life ruiner. Not Ruby. Ruby was the good girl...by comparison, anyway. Their father was a minister. Granted, Ruby had a handful of tattoos and a few piercings, she did, after all, work in a high end tattoo parlor, but she was still a good girl. The amount of shit Lilith got into wasn't even funny.

The small SUV pulled into the almost empty parking lot and Ruby blinked as a tall, buxom blonde emerged. Her eyes narrowed slightly and she kept her sunglasses in place, though it was now twilight. "Ruby?"

Ruby nodded. "Jessica?"

The blonde sniffed. "That's me."

Ruby worried her piercing again. "So...how do we do this?"

The blondes careful facade slipped. "Are you really..." She shook her head. "Did my Sammy..."

Ruby blew out a breath and nodded. "I swear, I didn't know he was married...if I had known..."

Jessica's eyes narrowed as she eyed Ruby. "I believe you."

"So...again, how do we...?"

Jessica blew out a breath. "Let's get a bite to eat. I'm starving. My forty-eight hour shift just ended. I need something besides something out of a vending machine or hospital food."

"You a nurse?"

"Pediatric surgeon."

Ruby blinked. "Why the fuck did he go slumming with me?" she wondered aloud. She winced. "Shit. Sorry."

Jessica shook her head. "Don't worry about it. You seem pretty damn nice, agreeing to meet me like this."

Ruby shrugged. "Why not? What do I have to lose?" She thought of the secret she was harboring and sighed. "I could eat."

They walked across the parking lot to the bar and slid into a booth. The bored looking waitress came up and asked, "What can I get ya?"

Jessica, it seemed, had been there before, because she boldly stated, "I'll have a sirloin, bloody rare, steak fries, Michelob Ultra. And whatever she wants."

The thought of that bloody steak made Ruby a little nauseated, but she said, "Fries. And a Sprite, please."

Jessica looked at her funny, but smiled at the waitress. "That'll do it for now. Thanks." Jessica watched the woman walk away then looked at Ruby. "So, I don't know what I'm doing. I don't like knowing what I'm doing."

Ruby chortled. "Yeah, I feel ya." She eyed the blonde again. "You're gorgeous, by the way."

Jessica smiled. "As are you. Although, Sam's always had an eye for the ladies. Everyone always talked about Dean, how he was the man whore. And maybe in high school, he was. But he met Lisa, and she became his best friend. They got together at their senior prom. They went to college together. Then, their senior year of college, she got pregnant. Ben's great. So is Gabriel, though he's a handful. A few years ago, they had baby Emma, well, she's not a baby anymore."

"Do you and Sam..." Ruby couldn't form the words.

Luckily, Jessica seemed to know what she was asking. "No. Being a surgeon...it's all I've ever wanted. All Sam ever wanted to be was a lawyer. Kids were never in the cards for us. His "sister", Jo has a couple of kids, and then Dean has the three...but, no, we didn't want kids. Maybe in another life..." She blew out a breath.

Ruby swallowed. Well, that made things...easier, she supposed. "So, we've met. Now what?"

Jessica's blue eyes turned almost black in anger. "Now I'm pissed. No one screws around on me and gets away with it."

"Yeah, but, I mean, it's not like we can kill him..."

Jessica sent her a cold smile. "Oh, that's exactly what I'm proposing."

Ruby's eyes widened as the waitress brought their drinks. The rolling nausea working its way through her had nothing to do with the child she carried, and everything with the implications of getting caught. "Jessica...I...I can't. I'm..."

"Pregnant. I know."

Both Ruby's hands shot to her mouth. "How did you...?"

Jessica shrugged. "I'm good at reading people. And the color green you were sporting as I mentioned how I wanted my steak cooked was a pretty damn good indication." She looked Ruby up and down. "Well, you must be a damn good lay for him to forget to be careful."

"He was. I mean, we were, I mean..." Ruby sighed. "It just happened."

"Are you keeping it?""

Ruby just glared. She might not be as religious as her dad wanted her to be, but she was a pro-lifer. She didn't believe in abortion. Besides that, even if Sam didn't, or rather, hadn't loved her, she'd loved him, somewhat, anyway. "Of course I am! But I don't want anything from Sam or you. I'll...I'll keep it quiet and then I won't put his name on the birth certificate. I swear it."

Jessica swigged her beer. "Whatever you want is fine. Sam won't be alive to do anything about it."

"Are you really going to..."

"You're damn right I am. And if you refuse to help me, you'd better be smart enough not to say anything."

Ruby swallowed. She'd been threatened before. Sometimes people didn't mean it. But this woman? She was guano. She meant it. "I won't tell a soul."

"Good."

"Can...can I ask how?"

Jessica's eyes narrowed and that smile was evil. "His car. It was his dad's Impala. Only thing that miserable son of a bitch left them. Dean had it forever, but when Lisa got knocked up with Gabe, money was tight, Sam begged to buy it so Dean could afford a family car. He and Dean work on it together. I've helped. I know exactly how to handle it so it has a problem. One that will take care of him."

Ruby swallowed. "Oh-okay." She couldn't stand to look at this woman anymore. "I...I gotta go. I have an appointment."

Jessica pointed a manicured finger at her as the waitress returned. "Remember what I said, Ruby."

Ruby just nodded before she practically ran out of the bar.

She got back to the safety of her classic caddy, a gift from Sam, actually, and drove off as fast as she dared.

* * *

She didn't know what she expected, but two days later, Sam texted her. YOU WANT SOME? was the only words on the text.

She blinked. What did she do? How should she...? Just them she got a text from another number; "It's Jess. We just had a fight. If he calls you, you'd better not let on about our plan."

Ruby swallowed and blew out a breath. She sent a text back to Sam; "Sure, baby. Come to my place." She was going to tell him. Sam would protect her, wouldn't he?

While she waited, she straightened up her modest place. She would need to find somewhere better to live. Her kid couldn't grow up here. It would need good schools and good friends and...she blew out a breath. She was gonna have to go home. She couldn't do this without help. Unless...maybe if Sam...if he was miserable enough to cheat on Jessica, maybe he'd leave her. Then Ruby could tell Sam about the baby, about how crazy Jessica was...

The knock on the door made her realize she had been standing, deep in thought, for the past ten minutes. She blinked and walked to the door.

"Hey," she said with a smile as she looked up at him. Sam Winchester was the most gorgeous specimen she'd ever seen. He was six feet, four inches of raw sex. He ran every morning and worked out religiously so he was all sinew and muscle with perfect definition all over his whole body. If only he wasn't such a dick, he'd be perfect.

He didn't even respond as he picked her up, wrapped her legs around his waist and began ravaging her.

Usually, she liked the fact the man acted like a caveman when they had sex, but she wanted to talk to him, to see how he'd feel...

She tried to push away, push him away, but he turned her so she was against the wall. "Sam..." she began.

"Not now. I've got an itch only you can scratch..." he growled as he carried her to the bedroom and tossed her none too gently to the bed.

"Sam..."

He looked at her then, those damn puppy dog eyes making her almost forget her own name. "Ruby, please, I need this."

Those moments, when he showed his vulnerability, that's why she'd fallen in love with him. She put both of her hands on his face. "Okay."

Sam was, without a doubt, one of the best lovers she'd ever had. He was also one of the roughest, and she'd spent more than a few nights soaking in a tub of hot water and wincing for days after their trysts. It had always been worth it. But now, with the baby, and with Jessica's crazy ass...Ruby knew she needed more.

"Hey, Sam?" she asked as he slid his pants back up his legs once he'd finished.

"Yeah, babe?"

She licked her lips nervously as she sat up and wrapped the sheet around herself, slipping on a sleep shirt as she did so. Some co versa turns required clothing, and this was going to be one of them. "Um...where do you see this going?"

He didn't even turn around as he slid his shirt up his arms. "See...what going?"

"Us."

He smiled and sat on the edge of the bed as he began buttoning his shirt. "Isn't what we have good enough?"

She debated how to say it, before she finally blurted out, "I'm pregnant, Sam."

Those hazel eyes, so often warm and sweet, even when he was acting like a jerk, turned cold as ice. "What?"

"I'm pregnant. Only a few weeks..."

His jaw ticked. "Is it mine?"

She slapped his face. "Fuck you, Sam. Of course it's yours!"

"Well how the hell am I supposed to know? Some tatted up, pierced little floozy I'm currently fucking comes up and says she's pregnant, why would I think she'd be monogamous?"

She wouldn't cry, not now. Right now, she was pissed. "You arrogant, DICK!" she screamed as she threw her pillow (the closest thing she could reach) at him. She moved closer to hit him and he caught her wrist, squeezing it so hard, a tear leaked out as the pain raced through her.

"Do you know who I am? I'm Sam Fucking Winchester. And you? You're nothing. You're worth less than the dirt on my boot." He tossed her wrist away from him and stood. He grabbed his tie and suit jacket and stalked down the hall.

She ran after him and got in his path. "Sam, wait, please!"

He grabbed her, this time, by the throat, and shoved her into the wall. "Listen to me, you little gold digging bitch, I've got nothing for you. You hear me? Nothing! So get that taken care of, and forget I ever existed, you got it?"

Tears were streaming down her face now. "G-Got it," she wheezed.

He let go of her and she collapsed into a puddle on the ground. She didn't know how long she lay there sobbing, but when she got up, she went straight for her phone. She sent two simple words to Jessica's number. "I'M IN."

* * *

PRESENT DAY

Ruby arrived only moments after the Cadillac limousine with the family pulled in to the graveyard. They were having a graveside service for Sam. Ruby rubbed her slightly growing belly softly as she stood and walked to the back of the group. All of Sam's friends and family were there, the whole firm, a ton of people from the hospital Jessica worked at...it was a huge service.

The pastor spoke first, telling everyone what a good man Sam was, how he had been taken from them too soon, how God needed one of his angels back home. Ruby wasn't sure she believed all that crap, but it was comforting, she guessed.

Then Dean stood up. She knew Dean only because Sam talked about him all the time, how great a guy he was, how proud he was of his big brother for getting an electrical engineering degree, how awesome it was when Dean had made the cover of some big deal magazine for some invention that had made his family very comfortable with money, how much he loved his niece and nephews. Funny how he never mentioned a wife, but a brother, he talked incessantly about.

Dean was teary eyed as he said, "My baby brother was one of the best men I knew." Ruby tried not to snort. If Dean only knew what Sam really was... "He was a great lawyer, working his way up the corporate ladder, he was a great uncle, a humanitarian, always working at Habitat for Humanity houses when he had time, and he was a loving husband." Ruby's eyes caught Jessica's. It was funny, while their dresses weren't similar, they were both wearing hats that had little black veils on them. She had taken out her piercings, covered her tattoos, and was wearing a modest dress that concealed her baby bump. She looked like what Sam would have wanted, could have wanted...

She allowed herself one tear to fall down her cheek before she locked it up. Sam hadn't wanted her, hadn't wanted their child. Hadn't even wanted a happy life with his wife. She refused to feel sorry for her part in this. She had to think of the baby, the little boy growing within her. He would grow up to know how much his mama loved him. After all, there were worse things than living without a father.

When the service was coming to a close, the Priest offered a basket of roses to lay on the casket. She got in the line and received one. She walked over to where Dean was silently sobbing next to Sam's casket.

"He loved you, you know."

Dean swallowed and looked at her. "Do I know you?"

She shook her head. "My sister owns the coffee shop Sam stopped at daily. Our paths crossed a few times. He was always talking about you or your kids or your lovely wife."

Dean smiled. "Yeah?"

She nodded. "It's a shame. I know you must be so sad over losing someone who meant so much to you..."

He nodded. "Thank you, Miss...?"

"Hale. Ruby Hale. I just wanted to pay my respects before I left. I'm moving."

"Oh? Where to?"

She thought of the hundred thousand dollars Jessica had given her. It might have been blood money, but it would allow her and her son to have a good life somewhere. "Away from here," she stated finally. She put a hand on his arm, gave it a squeeze, then walked back to her car. As she was getting in, her eyes met Jessica's. They gave one another a small nod, a half smile, and the acknowledgment that their...relationship was now terminated. Ruby hadn't touched the car. Her hands might be dirty but her fingerprints were nowhere near the crime scene. She had a flight out to Grand Cayman booked for later in the afternoon. She was leaving and never looking back.

* * *

AN2: *crickets* ahem...so...yeah. There ya go. Sorry? Lol. Don't forget to leave a review in the way out...


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